Acetic Acid → 4-(3-Pyridylmethyl)benzoic acid methyl ester

HRID 1680026ノート

反応式

HRID 1680026 の反応式
COC(=O)/C=C/C1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:8][CH:7]=1.[C-:20]#N.[Na+].[C:23]([OH:26])(=[O:25])[CH3:24]>[O-2].[O-2].[Mn+4].CO>[CH3:20][O:25][C:23](=[O:26])[C:24]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:8][CH:7]=1

参加物

6

反応物 3

HCID 176Acetic AcidHCID 8929Sodium CyanideHCID 12882181(E)-3-[4-(3-Pyridylmethyl)phenyl]acrylic acid methyl ester

生成物 1

HCID 541209054-(3-Pyridylmethyl)benzoic acid methyl ester

試薬・触媒・溶媒 2

HCID 178418406HCID 178418406、化合物触媒HCID 887Methanol溶媒

実験手順

A mixture of 300 mg of the aldehyde (prepared as described in Reference Example 1), 370 mg of sodium cyanide, 3.0 g of manganese dioxide, 0.18 ml of acetic acid and 15 ml of methanol was stirred overnight at room temperature, filtered through a pad of infusorial earth, and the filtrate was concentrated under reduced pressure. To the residue was added a saturated aqueous solution of sodium bicarbonate, and extracted with chloroform. The extract was washed with water, dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (3:2) as eluent to give 255 mg of the title compound having the following physical characteristics:

後処理

  1. filtrationfiltered through a pad of infusorial earth
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the residue was added a saturated aqueous solution of sodium bicarbonate
  4. extractionextracted with chloroform
  5. washThe extract was washed with water
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel using
  9. additiona mixture of cyclohexane and ethyl acetate (3:2) as eluent

出典と根拠

ORDレコード
ord-58462923e4664a8c94ba55f27c362f32
出典データセット
uspto-grants-1981_06
特許番号
US04271170

反応ノート

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